EP3609476A1 - Pullulan capsules - Google Patents
Pullulan capsulesInfo
- Publication number
- EP3609476A1 EP3609476A1 EP18724311.8A EP18724311A EP3609476A1 EP 3609476 A1 EP3609476 A1 EP 3609476A1 EP 18724311 A EP18724311 A EP 18724311A EP 3609476 A1 EP3609476 A1 EP 3609476A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- oil
- capsule
- lecithin
- pullulan
- surfactant
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4816—Wall or shell material
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
Definitions
- Hard and soft capsules comprising pullulan are known.
- Pullulan provides a number of advantages over other conventional capsule film forming polymers such as gelatin or hydroxypropyl methyl cellulose.
- Pullulan is a natural product of non-animal origin made without the need for chemical modification. High product quality consistency can be obtained by controlling the fermentation process.
- the resulting films formed with pullulan have excellent homogeneity and transparency.
- such films have very low oxygen permeability.
- capsules made from pullulan are particularly useful for the filling of oxygen sensitive products such as fish and vegetable oils.
- Such films and resulting capsules made from pullulan also have relatively low water content, and exhibit high stability over storage, such as with respect to mechanical and dissolution properties.
- pullulan The natural origin of pullulan and its superior properties as a film forming material has made pullulan a desired polymer for the manufacture of capsules having ingredients of all natural origin. This would enable capsules made with pullulan to meet the requirements for "organic" labeling. Notwithstanding the commercial need for a capsule meeting the organic labeling requirements, no satisfactory pullulan capsules have to date been developed that meet the organic labeling requirements.
- a capsule consists essentially of: pullulan in an amount of at least
- wt% of the capsule 70wt% of the capsule; a setting system in an amount of at least 0.01 wt% of the capsule; and a surfactant selected from the group consisting of sucroglycerides, sugar fatty acid sugar esters, and mixtures thereof in an amount of at least 0.2wt% of the capsule.
- the wt% amounts are exclusive of water present in the capsule.
- the surfactant is a sucrose fatty acid ester.
- the surfactant is a sucroglyceride.
- the surfactant is derived from the fatty acids of coconut oil.
- the surfactant is sucrose cocoate.
- the surfactant is present in an amount of from 0.2wt% to 2wt% of the capsule composition, or from 0.4wt% to 1 .5wt% of the capsule composition, or from 0.5wt% to 1 wt% of the capsule composition (exclusive of water).
- the setting system comprises carrageenan, gellan or agar. In one embodiment, the setting system comprises carrageenan and cations. In another embodiment, the setting system comprises agar and cations.
- the capsules have a Ca2+ content of at least 200mg/kg, or at least
- the capsules have a Mg2+ content of at least 30mg/kg, or at least 40 mg/kg, or even at least 50mg/kg.
- the capsule further comprising plasticizers or/and flavoring agents.
- the capsule further comprises coloring agents in a range from about
- the capsule comprises a coating.
- a caplet is encapsulated in the capsule.
- a method for manufacturing the capsule of claim 1 or 2 comprises:
- the mold pins are lubricated with a mixture of lecithin and a vegetable oil.
- the mold pins are lubricated with a sucroglyceride or sugar fatty acid ester. In another embodiment, the mold pins a lubricated with a mixture of a sucroglyceride and lecithin.
- the lecithin is selected from the group consisting of soybean lecithin, peanut lecithin, cottonseed lecithin, sunflower lecithin, rapeseed lecithin, corn lecithin, and groundnut lecithin. In a preferred embodiment, the lecithin is sunflower lecithin.
- the vegetable oil is selected from the group consisting of coconut oil, palm oil, palmist oil, soy oil, rapeseed oil, sunflower oil, cottonseed oil, peanut oil, olive oil, canola oil, castor oil, corn oil, flaxseed oil, safflower oil, and sesame oil.
- the lubricant comprises a mixture of coconut oil and sunflower lecithin.
- w/w % and “wt%” means by weight as a percentage of the total weight.
- a composition comprises pullulan, a setting system, water and a surfactant system.
- a composition can contain from 75% to 95% by weight of pullulan, from 0.1 % to 15% by weight of the setting system, and from 0.2wt% to 3wt% of the surfactant.
- wt% is based on total weight of contents of the capsule exclusive of any water present in the composition.
- Pullulan is generally produced from starch by the fungus Aureobasidium pullulans. Pullulan has good film forming properties and a particularly low oxygen permeability. Its existence was reported for the first time in 1938. Hayashibara Company started the commercial production in 1976.
- the pullulan has low amounts of mono-, di-, and oligosaccharides.
- Pullulan can be made free of mono-, di-, and oligosaccharides either through a post-manufacturing process step (e.g. precipitation of the mono-, di-, and oligosaccharides from a sample of a commercial pullulan grade in ethanol) or from its very production, by choosing appropriate fermentation conditions.
- a post-manufacturing process step e.g. precipitation of the mono-, di-, and oligosaccharides from a sample of a commercial pullulan grade in ethanol
- the pullulan has an average molecular weight comprised between about 1 0 kDa to 1 ,000,000 kDa, preferably between 1 00 KDa and 750 KDa, more preferably between 200 KDa and 500 KDa.
- a 1 0 wt% aqueous solution of pullulan may have a viscosity of from 1 00mm 2 /s to 180mm 2 /s at30 °C.
- pullulan is manufactured using an organic fermentation process.
- the fermentation media contains calcium phosphate and magnesium chloride.
- the capsules have a Ca2+ content of at least 200mg/kg, or at least 300mg/kg, or even at least 500 mg/kg.
- the capsules have a Mg2+ content of at least 30mg/kg, or at least 40 mg/kg, or even at least 50mg/kg.
- the ratio of K+/(Mg2+ + Ca2+) is less than 50, or less than 40, or less than 30, or even less than 20.
- a setting system preferably based on polysaccharides
- pullulan solutions enables the adaptation of specific and desired gelling properties for the production of hard pullulan capsules by a conventional dipping process.
- the aqueous film forming pullulan solution from which the capsules are made remains on the mold pins after dipping, and does not flow down the pins. Otherwise the obtained film will not have the desired uniform thickness.
- the polysaccharides are selected from the group comprising alginates, agar gum, guar gum, locust bean gum (carob), carrageenan, tara gum, gum arabic, ghatti gum, Khaya grandifolia gum, tragacanth gum, karaya gum, pectin, arabian (araban), xanthan, gellan, starch, Konjac mannan, galactomannan, funoran, and other exocellular polysaccharides. Preferred are exocellular polysaccharides.
- Preferred exocellular polysaccharides for use in the present invention are selected from the group comprising xanthan, acetan, gellan, welan, rhamsan, furcelleran, succinoglycan, scleroglycan, schizophyllan, tamarind gum, curdlan, and dextran.
- the setting system is kappa-carrageenan with cations.
- the setting system is gellan gum with cations.
- the setting system is agar with cations.
- These setting systems produce high gel strength at low concentrations and have good compatibility with pullulan.
- the setting system may contain a cation containing salt.
- the cation containing salt in the setting system serves to enhance the setting ability of the gelling agents.
- the salt comprises cations such as K + , Li + , Na + , NH4 + , Ca 2+ , or Mg 2+ , etc.
- the amount of cations in the capsule is from 0.01 to 1 wt%, preferably less than 3wt%.
- the pullulan containing compositions further comprise a surfactant that is selected from the group consisting of sucroglycerides, sugar fatty acid esters, and mixtures thereof.
- the sucroglyceride is selected from the group consisting of coconut oil sucroglyceride, palm oil sucroglyceride, palmist oil sucroglyceride, soy oil sucroglyceride, rapeseed oil sucroglyceride, sunflower oil sucroglyceride, cottonseed oil sucroglyceride, palmist oil sucroglyceride, peanut oil sucroglyceride, olive oil sucroglyceride, canola oil sucroglyceride, castor oil sucroglyceride, corn oil sucroglyceride, flaxseed oil sucroglyceride, safflower oil sucroglyceride, and sesame oil sucroglyceride.
- a preferred sucroglyceride is coconut oil sucroglyceride, or sucrose cocoate.
- Sucrose cocoate is a thick liquid that is pale yellow in color and derived from the fatty acids in coconut oil.
- Sugar fatty acid esters are nonionic surfactants consisting of a sugar as the hydrophilic group and a fatty acid as lipophilic group. They are also referred to as sugar esters. In one embodiment, the only surfactants present in the composition are sugar fatty acid esters.
- Sugar ester fatty acids may be prepared from sugar and methyl and ethyl esters of food fatty acids by esterification in the presence of a catalyst or by extraction from the appropriate glyceride, such as from sucroglycerides.
- Exemplary sugars that may be used as the head group include monosaccharides such as glucose, fructose, and galactose, disaccharides such as sucrose, maltose, trehalose and lactose, and trisaccharides such as raffinose.
- Exemplary fatty acids that may be used as the lipophilic group include fatty acids having from 6 to 18 carbon atoms, including capyrlic acid (C8), decanoic acid (C1 0), lauric acid (C12), myristic acid (C14), palmitic acid (C1 6) and oleic acid (C18).
- the lipophilic group may be derived from the fatty acid esters from vegetable oils, such as those selected from the group consisting of coconut oil, palm oil, palmist oil, soy oil, rapeseed oil, sunflower oil, cottonseed oil, peanut oil, olive oil, canola oil, castor oil, corn oil, flaxseed oil, safflower oil, and sesame oil.
- the vegetable oil is coconut oil.
- the sugar fatty acid ester is a sucrose fatty acid ester.
- sucrose esters may be formed from combining sucrose with particular fatty acids, and include sucrose laurate, sucrose stearate, sucrose erucate, sucrose oleate, sucrose palmitate, sucrose myristate, sucrose behenate, and sucrose ricenoleate. It is to be understood that such sucrose esters include the mono-, di-, tri- and polyesters.
- the surfactant may also contain lecithin.
- the lecithin may be selected from any naturally occurring plant based source.
- the lecithin is selected from the group consisting of soybean lecithin, peanut lecithin, cottonseed lecithin, sunflower lecithin, rapeseed lecithin, corn lecithin, and groundnut lecithin.
- the lecithin is sunflower lecithin.
- the surfactant is present in an amount sufficient to aid in film formation on the mold pins during manufacturing. In one embodiment, the surfactant is present in an amount of at least 0.2wt% of the capsule composition (exclusive of water content). In one embodiment, the amount of surfactant is present in an amount of from 0.2wt% to 2wt% of the capsule composition, or from 0.4wt% to 1 .5wt% of the capsule composition, or from 0.5wt% to 1 wt% of the capsule composition (exclusive of water).
- the capsules also generally comprise between 2wt% and 20wt%, preferably between about
- a capsule of the invention is dried to water content between about 1 0wt% and
- water content can be brought to lower % by e.g. further drying, capsule shell storage at low relative humidity or filling the capsule with hygroscopic substances.
- the capsule composition may further comprise at least one sequestering agent.
- Sequestering agents may be selected from the group consisting of ethylenediaminetetraacetic acid, acetic acid, boric acid, citric acid, edetic acid, gluconic acid, lactic acid, phosphoric acid, tartaric acid, or salts thereof, methaphosphates, dihydroxyethylglycine, lecithin or beta cyclodextrin and combinations thereof.
- compositions preferably contain a sequestering agent to improve the capsule solubility.
- sequestering agents are sodium bicarbonate, sodium bicarbonate, sodium tartrate, sodium tartrate, sodium tartrate, sodium tartrate, sodium tartrate, sodium tartrate, sodium tartrate, sodium tartrate, sodium tartrate, sodium tartrate, sodium tartrate, sodium tartrate, sodium tartrate, sodium tartrate, sodium tartrate, sodium tartrate, sodium tartrate, sodium tartrate, sodium tartrate, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite
- ethylenediaminetetraacetic acid or salts thereof and citric acid and salts thereof The amount is preferably less than xwt% in the capsule compositions.
- the capsule compositions may optionally further include other minor components such as titanium dioxide and/or colorants such as mineral colorants, natural colorants, and tar colorants, anti-oxidants and the like.
- the pullulan composition optionally comprises one or more pharmaceutically or food acceptable plasticisers.
- the one or more plasticizers are selected in the group of plasticizers typically used in the manufacture of hard capsule shells and in particular in the group consisting of: phthalic esters (e.g. dimethyl-, diethyl-, dibutyl-, diisopropyl- and dioctyl-phtalate); citric esters (e.g. triethyl-, tributyl-, acetyltriethyl- and acetyltributyl-citrate); phosphoric esters (e.g.
- oils e.g. purified mineral oils, ricin oil, corn oil, cotton oil); butyl stearate; dibutyl sebacate; dibutyl tartrate; diisobutyl adipate, glycerol monostearate; glycerol triacetate; tributyrin; oleic acid; stearic acid; cetylic acid; myristic acid; propylene glycol; glycerol; PEG 4000, PEG 6000, and mixtures thereof.
- oils e.g. purified mineral oils, ricin oil, corn oil, cotton oil
- butyl stearate dibutyl sebacate; dibutyl tartrate; diisobutyl adipate, glycerol monostearate; glycerol triacetate; tributyrin; oleic acid; stearic acid; cetylic acid; myristic acid; propylene glycol; glycerol; PEG 4000,
- Capsules according to the present disclosure are typically made via a dip-molding process.
- aqueous dipping composition comprising pullulan, a setting system, and a surfactant that is a sucroglyceride, a sugar fatty acid ester or mixture thereof;
- Steps (a) to (f) are typically to be performed in the order they are presented.
- finished capsule shells are those capsule shells for which step (f) has been completed.
- the aqueous dipping composition is prepared by combining water, pullulan, the setting system, and the sugar fatty acid ester.
- the aqueous composition of the invention has a total amount of solids typically comprised between about 10% and 55% by weight, preferably between about 15% and 40%, more preferably between 20% and 30% by weight over the total weight of the composition.
- wt% is given based on the total weight of the aqueous dipping composition including water.
- the aqueous composition of the invention has a total amount of solids so that the viscosity of the aqueous dipping composition at a temperature comprised between about 50 ° C and 70 ° C is between about 500 cPs and 5000 cPs, preferably between about 1 000 to 3000 cps.
- the concentration of pullulan in the aqueous dipping composition is in a range of 1 0 to 60wt%, preferably 1 0 to 50wt%, more preferably 15 to 40wt%, and most preferably 1 0 to 40wt%.
- the amount of the setting system is preferably in the range of 0.01 to 5% by weight and especially preferred 0.03 to 1 .0% in the aqueous dipping composition.
- the preferred salt concentration in the aqueous dipping concentration is less than 2wt%.
- the amount of the optional sequestering agent is less than 5% by weight, preferably less than 3%, more preferably 0.01 % to 3% by weight, even more preferably 0.5% to 2% by weight especially 0.01 to 1 % by weight of the aqueous dipping composition.
- the aqueous dipping compositions may optionally further include other minor components such as titanium dioxide and/or colorants such as mineral colorants, natural colorants, and tar colorants, anti-oxidants and the like.
- the coloring agents, or mixtures thereof are present in an amount ranging from about 0 to about 5% by weight, e.g., from about 0 to about 2.5% by weight, and from about 0 to about 1 .5% by weight over the total weight of the aqueous dipping composition.
- step (b) mold pins are dipped in the aqueous dipping composition.
- the relative temperatures of the aqueous dipping composition and mold pins are chosen to result in film formation on the mold pins once the mold pins are dipped into the aqueous composition.
- the aqueous composition at the time the mold pins are dipped is kept at a temperature of from 45 °C to 65 °C, preferably from 50 °C to 65°C.
- the temperature range of the pins is 25-35 ' C, meaning that this is the mold pin temperature when mold pins are dipped.
- step (c) the mold pins are extracted from the aqueous dipping composition such that a film is formed over each of the mold pins.
- the mold pins can be turned from a "top- down" dipping position to a "top-up” drying position according to conventional capsule dip molding processes.
- the pins are rotated about a horizontal axis of about 180 ' with respect to the dipping position of step (c).
- step (d) the film on the mold pins is dried.
- the purpose of the drying step (d) is to reduce the water content (also referred to herein as "moisture") in the capsule shells on the mold pins.
- drying occurs at a temperature above the gelling temperature of the aqueous dipping composition so as to obtain molded capsule shells on the pins.
- the drying step is preferably carried out at a temperature of less than 65 °C, preferably less than 60 °C, even more preferably from 25 °C to 45 °C.
- Step (d) is typically carried out for a period of time from 30 to 60 minutes, preferably not exceeding the above identified temperatures.
- the water content in the molded capsule shells is reduced from around 80% to around 1 0 to 15% by weight, based on the total weight of the molded capsule shells (measured at room conditions).
- step (f) the solid coating is removed from the mold pins to provide capsule shells.
- the solid coating may be removed using any conventional manufacturing technique.
- the solid coating in step (e) and the mold pins may be lubricated.
- the lubricant enhances gliding of the capsule shells to facilitate filling and closing.
- the lubricant facilitates removal of the capsule shells.
- the lubricant used for the external application to the solid coatings and/or to the mold pins is selected from a mixture of lecithin and a vegetable oil.
- the lecithin may be selected from any naturally occurring plant based source.
- the lecithin is selected from the group consisting of soybean lecithin, peanut lecithin, cottonseed lecithin, sunflower lecithin, rapeseed lecithin, corn lecithin, and groundnut lecithin.
- the lecithin is sunflower lecithin.
- the vegetable oil may be selected from any naturally occurring vegetable oil.
- the vegetable oil is selected from the group consisting of coconut oil, palm oil, palmist oil, soy oil, rapeseed oil, sunflower oil, cottonseed oil, peanut oil, olive oil, canola oil, castor oil, corn oil, flaxseed oil, safflower oil, and sesame oil.
- the vegetable oil is coconut oil.
- the relative amount of lecithin to vegetable oil ranges from 90/10 lecithin/vegetable oil to
- the lubricant comprises a mixture of coconut oil and sunflower lecithin.
- the lubricant comprises a sucroglyceride or sugar fatty acid ester.
- the lubricant is a sucroglyceride, preferably sucrose cocoate.
- the lubricant comprises a sugar fatty acid ester derived from coconut oil.
- the lubricant may also optionally comprise lecithin in addition to the sucroglyceride or sugar fatty acid ester in a ratio of from 1 /99 to 50/50 lecithin/sucrose glyceride or lecithin/sugar fatty acid ester.
- the lubricant comprises a mixture of sucrose cocoate and sunflower lecithin in a ratio of from 1 /99 to 50/50 sunflower lecithin/sucrose cocoate. In one embodiment, the lubricant consists essentially of a mixture of sucrose cocoate and sunflower lecithin in a ratio of from 1 /99 to 50/50 sunflower lecithin/sucrose cocoate.
- the molded capsule shells mentioned to above generally refer to both bodies and caps, depending on the shape of the mold pin.
- the dried capsule shells on the dipping pins can be processed according to conventional steps. This means that in general after step (e), the capsule shells (bodies and caps) are stripped from the pins. This step can be followed by cutting the stripped shells to a desired length.
- the capsule compositions are suitable for use in pharmaceutical, veterinary, food, cosmetic or other products.
- Drugs i.e. medicaments suitable for use in the capsules described herein may take any form and be for any treatment of a human or animal subject. This includes not only pharmaceutical compounds but also dietary supplements such as vitamins, minerals and the like.
- the drug may be in a state selected from solid or liquid, preferably solid, at room temperature and atmospheric pressure, and comprises one or more active compounds.
- the medicament may be solid and in the form of spray dried dispersions, pellets, granules and the like.
- Suitable compounds (and generally encompassed by the term "medicament” as used herein) for delivery according to the disclosure include, but are not limited to, particulate, powder, waxy, liquid, and/or pellet forms of the following:
- a) pharmaceuticals such as betamethasone, thioctic acid, sotalol, salbutamol, norfenefrine, silymahn, dihydroergotamine, buflomedil, etofibrate, indomethacin, oxazepam, acetyldigitoxins, piroxicam, halopehdol, isosorbide mononitrate, amithptyline, diclofenac, nifedipine, verapamil, pyritinol, nitrendipine, doxy- cycline, bromhexine, methylprednisolone, clonidine, fenofibrate, allopurinol, pirenzepine, levothyroxine, tamoxifen, metildigoxin, o-(B-hydroxyethyl)-rutoside, propicillin, aciclo
- etofyllineclofibrate vincamine, cinnarizine, diazepam, ketoprofen, flupentixol, molsidomine, glibornuhde, dimethindene, melperone, soquinolol, dihydrocodeine, clomethiazole, clemastine, glisoxepid, kallidino- genase, oxyfedhne, baclofen, carboxymethylcystsin, thioredoxin, betahistine, 1 -tryptophan, myrtol, bromelain, prenylamine, salazosulfapyridine, astemizole, sulpiride, benzerazid, dibenzepin, acetylsalicylic acid, miconazole, nystatin, ketoconazole, sodium picosulfate, colestyramate, gemfibrozil, rifampin, fluocortol
- antiprotozoals vaccines, immunoglobulin, immunosuppressants, interferon, monoclonal antibodies, and mixtures thereof;
- vitamins e.g., fat-soluble vitamins such as vitamins A, D, E, and K, and water soluble vitamins such as vitamin C, biotin, folate, niacin, pantothenic acid, riboflavin, thiamin, vitamin B6, vitamin B12, and mixtures thereof;
- c) minerals such as calcium, chromium, copper, fluoride, iodine, iron, magnesium, manganese, molybdenum, phosphorus, potassium, selenium, sodium (including sodium chloride), zinc, and mixtures thereof;
- dietary supplements such as herbs or other botanicals, amino acids, and substances such as enzymes, organ tissues, glandulars, and metabolites, as well as concentrates, metabolites, constituents, extracts of dietary ingredients, oils such as krill oil and mixtures thereof;
- probiotics and yeast such as bacteria selected from the group consisting of Lactobacillus
- Doderlein's bacilli such as Lactobacillus crispatus, Lactobacillus jensinii, Lactobacillus johnsonii,
- drospirenone dydrogesterone, ethisterone (pregneninolone, 1 7a- ethynyltestosterone), ethynodiol diacetate, fluorogestone acetate, gastrinone, gestadene, gestodene, gestonorone, gestrinone,
- the capsules can be made tamper-proof by using any conventional technique in the field of hard capsules to make the joint permanent.
- Banding or sealing are suitable techniques. Sealing is a technique well known in the field of hard shell capsules. Various alternative techniques are currently used for this purpose. A suitable procedure is disclosed for example in US 4,539,060 and US 4,656,066.
- compositions comprising pullulan, a setting system, water and a sucroglyceride or sugar fatty acid ester may be used to form films.
- films may be used for a variety of other purposes, such as for wrapping food, or for forming aspics or jellies.
- Capsules were prepared using dip molding equipment. The aqueous dipping composition was heated to 65 °C. The pins were maintained at 30 °C.
- capsules produced from organic pullulan made according to Example 1 are produced from organic pullulan made according to Example 1
- Capsule A and Plantcaps® capsules from Capsugel, Greenwood, SC, (Capsule B) were analyzed for Mg2+ and K+ content using the standard protocol SM31 1 1 B using Flame Atomic Absorption Spectroscopy.
- Ca2+ content in these capsule was also measured using the standard protocol SM31 1 1 D using Flame Atomic Absorption Spectroscopy.
- Each capsule batch was analyzed in triplicate. From this analysis it was determined that the concentration of both Mg2+ and Ca2+ is higher in Capsule A than Capsule B.
- Capsule A capsules have a lower ratio of monovalent cation (K+) to divalent cations (Mg2+ and Ca2+).
Abstract
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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US201762485854P | 2017-04-14 | 2017-04-14 | |
PCT/IB2018/000448 WO2018189584A1 (en) | 2017-04-14 | 2018-04-10 | Pullulan capsules |
Publications (1)
Publication Number | Publication Date |
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EP3609476A1 true EP3609476A1 (en) | 2020-02-19 |
Family
ID=62152586
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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EP18724311.8A Pending EP3609476A1 (en) | 2017-04-14 | 2018-04-10 | Pullulan capsules |
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US (2) | US11576870B2 (en) |
EP (1) | EP3609476A1 (en) |
JP (2) | JP2020516653A (en) |
CN (1) | CN110678170A (en) |
AU (1) | AU2018251256B2 (en) |
BR (1) | BR112019021391A2 (en) |
CA (1) | CA3059527A1 (en) |
WO (1) | WO2018189584A1 (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US11319566B2 (en) | 2017-04-14 | 2022-05-03 | Capsugel Belgium Nv | Process for making pullulan |
US11576870B2 (en) | 2017-04-14 | 2023-02-14 | Capsugel Belgium Nv | Pullulan capsules |
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US10899849B2 (en) | 2019-04-30 | 2021-01-26 | Lefan Capsule International Inc | Method for the production of pullulan capsules |
US10894971B1 (en) * | 2019-06-26 | 2021-01-19 | Lefan Capsule International Inc | Method for the production of pullulan soft capsules |
CA3155876A1 (en) * | 2019-10-09 | 2021-04-15 | R.P. Scherer Technologies, Llc | Non-animal softgel capsule formulations, methods of preparation, and methods of use thereof |
CN112089701A (en) * | 2020-10-30 | 2020-12-18 | 华侨大学 | Vitamin E plant soft capsule shell and application thereof |
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AU2018251256B2 (en) | 2017-04-14 | 2023-10-05 | Capsugel Belgium Nv | Pullulan capsules |
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2018
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- 2018-04-10 BR BR112019021391A patent/BR112019021391A2/en unknown
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US11319566B2 (en) | 2017-04-14 | 2022-05-03 | Capsugel Belgium Nv | Process for making pullulan |
US11576870B2 (en) | 2017-04-14 | 2023-02-14 | Capsugel Belgium Nv | Pullulan capsules |
US11878079B2 (en) | 2017-04-14 | 2024-01-23 | Capsugel Belgium Nv | Pullulan capsules |
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CA3059527A1 (en) | 2018-10-18 |
BR112019021391A2 (en) | 2020-05-05 |
US20200289422A1 (en) | 2020-09-17 |
WO2018189584A9 (en) | 2019-01-17 |
JP2023052025A (en) | 2023-04-11 |
JP2020516653A (en) | 2020-06-11 |
US20230131084A1 (en) | 2023-04-27 |
AU2018251256B2 (en) | 2023-10-05 |
CN110678170A (en) | 2020-01-10 |
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AU2018251256A1 (en) | 2019-11-28 |
US11878079B2 (en) | 2024-01-23 |
WO2018189584A1 (en) | 2018-10-18 |
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